DK0385354T3 - Process for the preparation of anthracyclinones - Google Patents

Process for the preparation of anthracyclinones

Info

Publication number
DK0385354T3
DK0385354T3 DK90103707.7T DK90103707T DK0385354T3 DK 0385354 T3 DK0385354 T3 DK 0385354T3 DK 90103707 T DK90103707 T DK 90103707T DK 0385354 T3 DK0385354 T3 DK 0385354T3
Authority
DK
Denmark
Prior art keywords
formula
compound
group
vii
chem
Prior art date
Application number
DK90103707.7T
Other languages
Danish (da)
Inventor
Walter Cabri
Ilaria Candiani
Bernardinis Silvia De
Franco Francalanci
Original Assignee
Erba Carlo Spa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Erba Carlo Spa filed Critical Erba Carlo Spa
Application granted granted Critical
Publication of DK0385354T3 publication Critical patent/DK0385354T3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/38—Quinones containing —CHO or non—quinoid keto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Saccharide Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catalysts (AREA)

Abstract

Process for preparing anthracyclinones of general formula (I): <CHEM> wherein R represents a hydrogen atom or a COOR1 group in which R1 may be a hydrogen atom or an optionally substituted C1-C10 alkyl group, which are intermediates in the preparation of antitumor anthracycline glycosides, are prepared by: (i)(a) reacting a 4-demethyl-4-sulfonyl-7-deoxy-13-dioxolanyl daunomycinone of formula (V): <CHEM> wherein R min represents an alkyl group having from 1 to 10 carbon atoms optionally substituted by one or more halogen atoms or an aryl group optionally substituted by halogen, alkyl, alkoxy or nitro, in a reducing environment with a catalytic amount of a compound of formula (VIII): MLnL min m wherein M represents a transition metal atom, L and L min , which may be the same or different, each represent an anion or a neutral molecule and n and m may vary from 0 to 4, such as to obtain a compound of formula (VII): <CHEM> wherein R represents hydrogen; or (b) carbonylating a 4-demethyl-4-sulfonyl-7-deoxy-13-dioxolanyl daunomycinone of formula (V) as defined above, with carbon monoxide in the presence of a nucleophile R1OH wherein R1 is as defined above, an organic or inorganic base and as catalyst a compound of formula (VIII) as defined above, such as to obtain a compound of formula (VII) as shown above wherein R represents a COOR1 group; and (ii) introducing an alpha -hydroxy group at the 7-position and removing the 13-oxo protecting group by acid hydrolysis from the resultant compound of formula (VII). r
DK90103707.7T 1989-03-02 1990-02-26 Process for the preparation of anthracyclinones DK0385354T3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB898904794A GB8904794D0 (en) 1989-03-02 1989-03-02 Process for preparing anthracyclinones

Publications (1)

Publication Number Publication Date
DK0385354T3 true DK0385354T3 (en) 1993-05-17

Family

ID=10652605

Family Applications (1)

Application Number Title Priority Date Filing Date
DK90103707.7T DK0385354T3 (en) 1989-03-02 1990-02-26 Process for the preparation of anthracyclinones

Country Status (26)

Country Link
US (1) US5180758A (en)
EP (1) EP0385354B1 (en)
JP (1) JP2717023B2 (en)
KR (1) KR0171047B1 (en)
CN (1) CN1028518C (en)
AT (1) ATE88173T1 (en)
AU (1) AU636134B2 (en)
CA (1) CA2047748C (en)
CZ (1) CZ278804B6 (en)
DE (1) DE69001312T2 (en)
DK (1) DK0385354T3 (en)
ES (1) ES2055189T3 (en)
FI (1) FI92687C (en)
GB (1) GB8904794D0 (en)
HU (1) HU207705B (en)
IE (1) IE63571B1 (en)
IL (1) IL93559A (en)
MY (1) MY105260A (en)
NO (1) NO174546C (en)
NZ (1) NZ232681A (en)
PT (1) PT93317B (en)
RU (1) RU2077526C1 (en)
SK (1) SK278225B6 (en)
WO (1) WO1990009974A1 (en)
YU (1) YU47556B (en)
ZA (1) ZA901542B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AUPQ319799A0 (en) * 1999-10-01 1999-10-28 Institute Of Drug Technology Australia Limited Chemical methods
JP4688315B2 (en) * 2001-02-28 2011-05-25 メルシャン株式会社 Production of 4-demethoxydaunomycinone
US7053191B2 (en) * 2003-05-21 2006-05-30 Solux Corporation Method of preparing 4-R-substituted 4-demethoxydaunorubicin
ATE464280T1 (en) * 2004-08-23 2010-04-15 Sicor Inc SYNTHESIS OF IDARUBIN-AGLYCONE
US8357785B2 (en) * 2008-01-08 2013-01-22 Solux Corporation Method of aralkylation of 4′-hydroxyl group of anthracylins
US8846882B2 (en) 2011-04-29 2014-09-30 Synbias Pharma Ag Method of producing 4-demethoxydaunorubicin

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ224252A (en) * 1987-04-21 1991-09-25 Erba Carlo Spa An anthracycline glycoside and its preparation
GB8808475D0 (en) * 1988-04-11 1988-05-11 Erba Carlo Spa Process for preparing 4-demethoxydauno-mycinone
GB8818167D0 (en) * 1988-07-29 1988-09-01 Erba Carlo Spa Novel 4-substituted anthracyclinones & process for their preparation

Also Published As

Publication number Publication date
ATE88173T1 (en) 1993-04-15
CS9000958A2 (en) 1991-08-13
IE63571B1 (en) 1995-05-17
NO913382D0 (en) 1991-08-28
DE69001312D1 (en) 1993-05-19
HUT58033A (en) 1992-01-28
WO1990009974A1 (en) 1990-09-07
SK278225B6 (en) 1996-04-03
DE69001312T2 (en) 1993-07-22
YU39990A (en) 1991-10-31
PT93317A (en) 1990-11-07
RU2077526C1 (en) 1997-04-20
JP2717023B2 (en) 1998-02-18
ES2055189T3 (en) 1994-08-16
KR900014286A (en) 1990-10-23
NO913382L (en) 1991-08-28
IL93559A0 (en) 1990-11-29
IE900700L (en) 1990-09-02
FI92687B (en) 1994-09-15
EP0385354B1 (en) 1993-04-14
YU47556B (en) 1995-10-03
HU902357D0 (en) 1991-11-28
NZ232681A (en) 1991-04-26
JPH04503803A (en) 1992-07-09
GB8904794D0 (en) 1989-04-12
ZA901542B (en) 1990-12-28
CA2047748C (en) 1999-05-18
FI914053A0 (en) 1991-08-28
US5180758A (en) 1993-01-19
IL93559A (en) 1994-06-24
CN1028518C (en) 1995-05-24
CN1045259A (en) 1990-09-12
EP0385354A1 (en) 1990-09-05
FI92687C (en) 1994-12-27
CA2047748A1 (en) 1990-09-03
NO174546B (en) 1994-02-14
CZ278804B6 (en) 1994-07-13
HU207705B (en) 1993-05-28
AU636134B2 (en) 1993-04-22
PT93317B (en) 1996-01-31
NO174546C (en) 1994-05-25
MY105260A (en) 1994-09-30
KR0171047B1 (en) 1999-03-30
AU5184890A (en) 1990-09-26

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